She is an avid sailor and spent three months in 2008 sailing across the Atlantic Ocean and the Mediterranean Sea.[6][7] In 2011, she embarked on a two-month expedition from Guatemala, travelling around Central America to Costa Rica.[8]

Werbowy had never seriously considered modeling, but found herself launched into the business after meeting a schoolmate's mother who headed Toronto's Susan J. Model & Talent Management. At age 14, Werbowy won a national modelling contest.[4]

After switching to Elite Model Management, Werbowy landed several prominent bookings in Canada but achieved little international success. Werbowy lived in London and Greece, where she did not find much work. Her first runway season was disrupted and her bookings canceled due to the 9/11 attacks in New York City.[6] Thus she went to Europe. After an exhausted eight months, Werbowy returned to Canada. She gave modeling a final shot as a means to fund her art school education.[6] "I returned to New York, met my agent and the next day I had an exclusive deal with Prada. From then on it was all a bit of a blur."[6]

When the Elite Canada's head scout, Elmer Olsen, started his own agency, Werbowy followed and her career began to flourish. Within a few years, and under the guidance of International Management Group (IMG), Werbowy gained a foothold on the international modelling stage.

Though she relinquished the world's No. 1 runway model status to new "it girls", Werbowy holds the record for opening and closing the most shows in one season. In her first season, Fall/Winter 2003, Werbowy captured two of the modeling world's most coveted assignments: the cover of Vogue Italia, thrice (in July, August and October), and Prada's Fall/Winter ad campaign.[9]

She ranked No. 6 on Forbes' "The World's Top-Earning Models" list, with estimated earnings of $4.5 million between May 2010 and May 2011.[18]

In 2015, Werbowy fronted campaigns for Equipment, Salvatore Ferragamo and H&M. She also featured on the March and June covers of Vogue Paris. Werbowy ranked no.12 on the 2015 Forbes list of highest earning models, earning an estimated $4.5 million.[19]